Azo dyestuffs and process of preparing them



Patented May 13,- 1930 UNITED STATES PATENT OFFICE EERZMLANN ,wAsnna, or 'SObEN-bN-THE-TAUNUS, nnmz nrcnwnnn AND ERIOH FISCHER, or HOCHST-ON-THE-MAIN,GERMANY, ASSIGNORS ro GENERAL Amnmn WORKS, INC., OF NEW YORK, N. Y., A

RP'ORATION on DELAWARE AZO-DYESTUFFS AND rnoonss or PREPARING 'rnnm Ho Drawing. -Application filed March 16, 1927, Serial No. 175,924, and in Germany March 31, 1926.

The ipresent invention relates to new azo dyestu s of the general formula:

I N CO wherein Y denotes the residue of any car- CH COO wherein Y, R, X and R have the same significance as in the previous formula.

The pyrazolone compounds to be used as coupling components ma be prepared, for

instance, by causing c loro-formic ester chloroacetic ester or a similar bod to actupon the corresponding aminoary pyrazo-' lones, if required, while adding an acid-binding agent as chalk or the like.

- The following examples serve to illustrate our invention but they are not intended to limit it thereto; the parts are by wei ht:

(1) 261 parts of the body .of the fo lowing formula H-N-OOOCnHu are dissolved in the cold in about 1000' parts of water while adding an equivalent quantity of an alkali, and the solution so obtained is neutralized with acetic acid. After having added to this solution about 180 parts of crystallized sodium acetate, there is run into the coupling liquid thus prepared a diazo solution obtained in known manner from 173 parts of ortho-aniline-sulfonicacid. The finished dyestufi' separates in the course of the coupling process. It forms, when filtered and drled, a yellow powder easily soluble in water, which has the formula:

The dyestufl' not only gives on wool yellow dyeings of excellent properties as to fastness, but it is particularly distinguished by its property of dyeing mixed textile goods made of wool and silk fibres very evenly and in an equal shade.

(2) 275 parts of the body of the formula:

for example sodium acetate,

are worked up as indicated in Example 1 and combined with a diazo solution prepared from 173 parts of sulfanilic acid. After having stirredthe reaction mass thus obtained for one or two hours, the dyestuif which has precipitated' is filtered by suction and dried. It

also forms a yellow powder easily soluble in water and having slmilar properties as the dyestufi obtained according to Example 1.

It has the following formula: I

HN=CH:COOO:Hs

The pyrazolones and the diazo compounds above specified may be largely varied. The new pyrazolones may also be used as valuable coupling components in thepreparation of disand poly-azo-dyestufls.

If the dyestuffs are intended to be used for the preparation of very even tints on mixed textile goods made of wool and silk fibres, the

combinations are advantageously selected in such a manner, that the dyestuff molecule.

does not contain more acid groups than are necessary for rendering the dyestuff soluble.

If anthranilic acid, ortho-aminophenol or derivatives of these compounds are used as diazo components, the dyestuffs or dyeings thus produced can be developed in known manner by afterchroming.

We claim:

1. The process of preparing azo dyestufis which are particularly suitable for dyeing mixed textile goods made of wool, and silk,

fibres, 'Which consists in coupling any aromatic diazo compound with a pyrazolone of the following general formula:

wherein Y stands for a carboxylic acid ester f residue.

3. The process ofpreparing azo dyestuffs which are particularly suitable for dyein mixed textile goods made of wool and silt fibres, which consists in coupling any aromatic diazo compound with the pyrazolone of the following formula:

4. The process of preparing an azodyestuff which is particularly suitable for dyeing mixed textile goods made of wool and silk fibres, which consists in coupling the diazo compound of ortho-aniline-sulfonic acid with the pyrazolone of the following formula:

H-N-oooonn 5. As new products azo dyestuffs of the general formula:

wherein Y stands for a carboxylic acid ester residue, R andR stand for aryl residues which may be substituted, X stands for hydrogen, alkyl, aryl or aralkyl, and R for CH COGH or COO-alkyl, said dyestuffs being particularly suitable for dyeing mixed textile goods made of wool and silk fibers.

6. As new products azo dyestuffs of the formula:

I N-oooo,m

wherein R and R stand for aryl residues which may be substituted, X stands for hydrogen, alkyl,,aryl or aralkyl, and R for CH COOH or COO-alkyl, said dyestufi's being particularly suitable for dyeing textile goods made of Wooland silk fibers.

7. As new products azo dyestuffs of the formula:

wherein R stands for an aryl residue which may be substituted, said dyestuff being particularly suitable for dyeing textile goods made of wool and silk fibers.

8. As a new product the azo dyestufl? of the formula: 1

said dyestuff being particularly suitable for dyeing mixed textile goods made of wool and silk fibers yellow shades. v

" In, tes timonywhereof, we aflix our signatures.

' HERMANN' WAGNER.

HEINZ EIGHWEDE. ERICH FISCHER. 

